Enzymatic preparation of heparin oligosaccharides containing antithrombin III binding sites.

The Journal of Biological Chemistry
T ToidaR J Linhardt

Abstract

Two new oligosaccharides were prepared from heparin by its partial depolymerization using heparin lyase I (EC 4.2.2.7) in an attempt to prepare oligosaccharides having intact antithrombin III binding sites. The oligosaccharides were purified by chromatography on the basis of both size and charge and demonstrated a high level of purity by capillary electrophoresis. One- and two-dimensional 1H NMR spectroscopy at 500 MHz revealed the structure of each oligosaccharide. The octasaccharide and decasaccharide are DeltaUAp2S(1-->4)-alpha-DGlcNpS6S(1-->4)-alpha-L-IdoAp (1-->4)-alpha-D -GlcNpAc6S(1-->4)-betaD-GlcAp(1-->4)-alpha-D-GlcNpS 3S6S(1-->4)-alpha- L-IdoAp2S(1-->4)alpha-D-GlcNpS6S (where DeltaUAp is 4-deoxy-alpha-L-threo-hex-enopyranosyluronic acid, GlcNp is 2-amino-2-deoxy-glucopyranose, GlcAp is glucopyranosyluronic acid, S is sulfate and Ac is acetate) and DeltaUAp2S(1-->4)-alpha-D-GlcNpS6S(1-->4)-alpha-L-IdoAp++ +(1-->4)-alpha- D-GlcNpAc6S (1-->4)-beta-D-GlcAp(1-->4)-alpha-D-GlcNpS3S6S(1-->4)-alpha- L-IdoAp2S (1-->4)-alpha-D-GlcNpS6S(1-->4)-alpha-L-IdoAp2S(1-->4)-alpha -D-GlcNpS 6S, respectively. A hexasaccharide containing a similar structural motif to that found in the antithrombin III binding site and having greatly reduce...Continue Reading

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Citations

Feb 22, 2002·Biomedical Chromatography : BMC·Wenjun MaoRobert J Linhardt
Dec 31, 2003·Methods : a Companion to Methods in Enzymology·Philip A PatstonSteven T Olson
Aug 25, 2006·Journal of Virology·Heidi BarthThomas F Baumert
Sep 14, 2000·Proceedings of the National Academy of Sciences of the United States of America·Z ShriverR Sasisekharan
Sep 14, 2000·Proceedings of the National Academy of Sciences of the United States of America·M A Nugent
Sep 14, 2000·Proceedings of the National Academy of Sciences of the United States of America·Z ShriverR Sasisekharan
Feb 25, 2014·Analytical Biochemistry·Pierre A J MourierChristian Viskov
Aug 26, 2014·Glycoconjugate Journal·Marco GuerriniChristian Viskov
Mar 19, 2014·Journal of Pharmaceutical Sciences·Li FuRobert J Linhardt
Mar 19, 2013·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Hengchang ZangFengshan Wang
Jun 28, 2001·Preparative Biochemistry & Biotechnology·Y S KimR J Linhard
Oct 20, 2004·Angewandte Chemie·Sarah R HansonChi-Huey Wong
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